U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C28H29F2N3O
Molecular Weight 461.5462
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PIMOZIDE

SMILES

FC1=CC=C(C=C1)C(CCCN2CCC(CC2)N3C(=O)NC4=CC=CC=C34)C5=CC=C(F)C=C5

InChI

InChIKey=YVUQSNJEYSNKRX-UHFFFAOYSA-N
InChI=1S/C28H29F2N3O/c29-22-11-7-20(8-12-22)25(21-9-13-23(30)14-10-21)4-3-17-32-18-15-24(16-19-32)33-27-6-2-1-5-26(27)31-28(33)34/h1-2,5-14,24-25H,3-4,15-19H2,(H,31,34)

HIDE SMILES / InChI

Molecular Formula C28H29F2N3O
Molecular Weight 461.5462
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/10762666

Pimozide (Orap) is a diphenylbutylpiperidine that is effective as an antipsychotic agent and as an alternative to haloperidol for the suppression of vocal and motor tics in patients with Tourette syndrome. It is not intended as a treatment of first choice nor is it intended for the treatment of tics that are merely annoying or cosmetically troublesome. It should be reserved for use in Tourette’s Disorder patients whose development and/or daily life function is severely compromised by the presence of motor and phonic tics. Evidence supporting approval of pimozide for use in Tourette’s Disorder was obtained in two controlled clinical investigations, which enrolled patients between the ages of 8 and 53 years. Most subjects in the two trials were 12 or older. Pimozide is an orally active antipsychotic drug product, which shares with other antipsychotics the ability to blockade dopaminergic receptors on neurons in the central nervous system. Although its exact mode of action has not been established, the ability of pimozide to suppress motor and phonic tics in Tourette’s Disorder is thought to be a function of its dopaminergic blocking activity. However, receptor blockade is often accompanied by a series of secondary alterations in central dopamine metabolism and function which may contribute to both pimozide’s therapeutic and untoward effects. In addition, pimozide, in common with other antipsychotic drugs, has various effects on other central nervous system receptor systems which are not fully characterized.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
18.0 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
ORAP

Approved Use

INDICATIONS & USAGE Pimozide Tablets, USP is indicated for the suppression of motor and phonic tics in patients with Tourette’s Disorder who have failed to respond satisfactorily to standard treatment. Pimozide Tablets, USP is not intended as a treatment of first choice nor is it intended for the treatment of tics that are merely annoying or cosmetically troublesome. Pimozide Tablets, USP should be reserved for use in Tourette’s Disorder patients whose development and/or daily life function is severely compromised by the presence of motor and phonic tics. Evidence supporting approval of Pimozide Tablets, USP for use in Tourette’s Disorder was obtained in two controlled clinical investigations which enrolled patients between the ages of 8 and 53 years. Most subjects in the two trials were 12 or older.

Launch Date

4.60079989E11
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
0.261 mg × h/L
2 mg single, oral
dose: 2 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PIMOZIDE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
0.347 mg × h/L
2 mg single, oral
dose: 2 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PIMOZIDE plasma
Homo sapiens
population: UNHEALTHY
age: CHILD
sex: MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
109 h
2 mg single, oral
dose: 2 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PIMOZIDE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
57 h
2 mg single, oral
dose: 2 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PIMOZIDE plasma
Homo sapiens
population: UNHEALTHY
age: CHILD
sex: MALE
food status: FASTED
Doses

Doses

DosePopulationAdverse events​
6 mg 1 times / day single, oral
Overdose
Dose: 6 mg, 1 times / day
Route: oral
Route: single
Dose: 6 mg, 1 times / day
Sources:
healthy, 1.5
n = 1
Health Status: healthy
Age Group: 1.5
Sex: F
Population Size: 1
Sources:
Other AEs: Tremor, Tongue thrust...
Other AEs:
Tremor
Tongue thrust
Drooling
Drowsiness
Slow response to stimuli
Blood pressure decreased
Sources:
100 mg 1 times / day single, oral
Overdose
Dose: 100 mg, 1 times / day
Route: oral
Route: single
Dose: 100 mg, 1 times / day
Sources:
healthy, 17
n = 1
Health Status: healthy
Age Group: 17
Sex: F
Population Size: 1
Sources:
Other AEs: Tremor...
0.2 mg/kg 1 times / day multiple, oral
Recommended
Dose: 0.2 mg/kg, 1 times / day
Route: oral
Route: multiple
Dose: 0.2 mg/kg, 1 times / day
Sources:
unhealthy, 2-13
n = 20
Health Status: unhealthy
Condition: Tourette's syndrome
Age Group: 2-13
Sex: M+F
Population Size: 20
Sources:
Disc. AE: Akathisia, Akinesia...
AEs leading to
discontinuation/dose reduction:
Akathisia
Akinesia
Sources:
800 mg 1 times / day single, oral
Overdose
Dose: 800 mg, 1 times / day
Route: oral
Route: single
Dose: 800 mg, 1 times / day
Sources:
healthy, 53
n = 1
Health Status: healthy
Age Group: 53
Sex: F
Population Size: 1
Sources:
Other AEs: Torsades de pointes, Electrocardiogram QTc interval prolonged...
Other AEs:
Torsades de pointes
Electrocardiogram QTc interval prolonged
Sources:
21 mg 1 times / day multiple, oral
Highest studied dose
Dose: 21 mg, 1 times / day
Route: oral
Route: multiple
Dose: 21 mg, 1 times / day
Sources:
unhealthy, adult
n = 51
Health Status: unhealthy
Condition: chronic schizophrenia
Age Group: adult
Sex: M+F
Population Size: 51
Sources:
AEs

AEs

AESignificanceDosePopulation
Blood pressure decreased
6 mg 1 times / day single, oral
Overdose
Dose: 6 mg, 1 times / day
Route: oral
Route: single
Dose: 6 mg, 1 times / day
Sources:
healthy, 1.5
n = 1
Health Status: healthy
Age Group: 1.5
Sex: F
Population Size: 1
Sources:
Drooling
6 mg 1 times / day single, oral
Overdose
Dose: 6 mg, 1 times / day
Route: oral
Route: single
Dose: 6 mg, 1 times / day
Sources:
healthy, 1.5
n = 1
Health Status: healthy
Age Group: 1.5
Sex: F
Population Size: 1
Sources:
Drowsiness
6 mg 1 times / day single, oral
Overdose
Dose: 6 mg, 1 times / day
Route: oral
Route: single
Dose: 6 mg, 1 times / day
Sources:
healthy, 1.5
n = 1
Health Status: healthy
Age Group: 1.5
Sex: F
Population Size: 1
Sources:
Slow response to stimuli
6 mg 1 times / day single, oral
Overdose
Dose: 6 mg, 1 times / day
Route: oral
Route: single
Dose: 6 mg, 1 times / day
Sources:
healthy, 1.5
n = 1
Health Status: healthy
Age Group: 1.5
Sex: F
Population Size: 1
Sources:
Tongue thrust
6 mg 1 times / day single, oral
Overdose
Dose: 6 mg, 1 times / day
Route: oral
Route: single
Dose: 6 mg, 1 times / day
Sources:
healthy, 1.5
n = 1
Health Status: healthy
Age Group: 1.5
Sex: F
Population Size: 1
Sources:
Tremor
6 mg 1 times / day single, oral
Overdose
Dose: 6 mg, 1 times / day
Route: oral
Route: single
Dose: 6 mg, 1 times / day
Sources:
healthy, 1.5
n = 1
Health Status: healthy
Age Group: 1.5
Sex: F
Population Size: 1
Sources:
Tremor
100 mg 1 times / day single, oral
Overdose
Dose: 100 mg, 1 times / day
Route: oral
Route: single
Dose: 100 mg, 1 times / day
Sources:
healthy, 17
n = 1
Health Status: healthy
Age Group: 17
Sex: F
Population Size: 1
Sources:
Akathisia Disc. AE
0.2 mg/kg 1 times / day multiple, oral
Recommended
Dose: 0.2 mg/kg, 1 times / day
Route: oral
Route: multiple
Dose: 0.2 mg/kg, 1 times / day
Sources:
unhealthy, 2-13
n = 20
Health Status: unhealthy
Condition: Tourette's syndrome
Age Group: 2-13
Sex: M+F
Population Size: 20
Sources:
Akinesia Disc. AE
0.2 mg/kg 1 times / day multiple, oral
Recommended
Dose: 0.2 mg/kg, 1 times / day
Route: oral
Route: multiple
Dose: 0.2 mg/kg, 1 times / day
Sources:
unhealthy, 2-13
n = 20
Health Status: unhealthy
Condition: Tourette's syndrome
Age Group: 2-13
Sex: M+F
Population Size: 20
Sources:
Electrocardiogram QTc interval prolonged
800 mg 1 times / day single, oral
Overdose
Dose: 800 mg, 1 times / day
Route: oral
Route: single
Dose: 800 mg, 1 times / day
Sources:
healthy, 53
n = 1
Health Status: healthy
Age Group: 53
Sex: F
Population Size: 1
Sources:
Torsades de pointes
800 mg 1 times / day single, oral
Overdose
Dose: 800 mg, 1 times / day
Route: oral
Route: single
Dose: 800 mg, 1 times / day
Sources:
healthy, 53
n = 1
Health Status: healthy
Age Group: 53
Sex: F
Population Size: 1
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG


OverviewOther

Other InhibitorOther SubstrateOther Inducer





Drug as perpetrator​Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
major
minor
minor
yes (co-administration study)
Comment: coadministration with paroxetine resulted in a 151% increase in pimozide AUC and 62% increase in pimozide Cmax.
Page: 9, 10, 15
yes
PubMed

PubMed

TitleDatePubMed
The effect of 5-hydroxytrytamine synthesis inhibitors on neuroleptic-induced catalepsy in rats.
1975
Ascending catecholamine pathways and amphetamine-induced locomotor activity: importance of dopamine and apparent non-involvement of norepinephrine.
1975 Aug 15
Antagonistic effect of cyproheptadine on neuroleptic-induced catalepsy.
1975 Jan-Feb
Catecholamine correlates of isolation-induced aggression in mice.
1975 Mar
Use of pimozide in the Pisa syndrome.
1992 Aug
Pharmacological options for the treatment of Tourette's disorder.
2001
Delusions of parasitosis. A dermatologist's guide to diagnosis and treatment.
2001
Comparative safety of the different macrolides.
2001
[Testosterone modulation of HERG potassium channel blockade induced by neuroleptics].
2001
Psychogenic excoriation. Clinical features, proposed diagnostic criteria, epidemiology and approaches to treatment.
2001
Tourette syndrome: clinical characteristics and current management strategies.
2001
The antipsychotic drugs sertindole and pimozide block erg3, a human brain K(+) channel.
2001 Aug 24
Gilles de la Tourette syndrome in a child with congenital deafness.
2001 Dec
Low-voltage-activated calcium channels are not involved in capacitation and biological response to progesterone in human sperm.
2001 Dec
Agonist, antagonist, and inverse agonist properties of antipsychotics at human recombinant 5-HT(1A) receptors expressed in HeLa cells.
2001 Dec 14
Pimozide (Orap) prolongs cardiac repolarization by blocking the rapid component of the delayed rectifier potassium current in native cardiac myocytes.
2001 Jul
Plasma steroids in mature common dentex (Dentex dentex) stimulated with a gonadotropin-releasing hormone agonist.
2001 Jul
The role of dopamine in the timing of Pavlovian conditioned keypecking in ring doves.
2001 Jul-Aug
Ophthalmic manifestations of Gilles de la Tourette syndrome.
2001 Jul-Sep
Further characterization of 5-HT1A receptors in the goldfish retina: role of cyclic AMP in the regulation of the in vitro outgrowth of retinal explants.
2001 Mar
Antipsychotic drugs: prolonged QTc interval, torsade de pointes, and sudden death.
2001 Nov
Re-evaluating the Na(+) conductance of adult rat alveolar type II pneumocytes: evidence for the involvement of cGMP-activated cation channels.
2001 Nov 1
Evidence for the involvement of dopamine D(1) and D(2) receptors in mediating the decrease of food intake during repeated treatment with amphetamine.
2001 Nov-Dec
[3H]dofetilide binding to HERG transfected membranes: a potential high throughput preclinical screen.
2001 Oct 26
Effects of dopaminergic and cholinergic interactions on rat behavior.
2001 Oct 5
Cavernous hemangioma in a child presenting with hemichorea: response to pimozide.
2001 Sep
[Therapy of subclinical (subdiagnostic) syndromes of schizophrenia spectrum].
2001 Sep
Antipsychotic-related QTc prolongation, torsade de pointes and sudden death.
2002
Effects of psychotropic drugs on seizure threshold.
2002
The effects of naltrexone, an opioid receptor antagonist, on plasma LH levels in common carp (Cyprinus carpio L.).
2002 Apr
In vitro inhibition of pimozide N-dealkylation by selective serotonin reuptake inhibitors and azithromycin.
2002 Apr
The Ca(2+) channel antagonists mibefradil and pimozide inhibit cell growth via different cytotoxic mechanisms.
2002 Aug
A comparison of the receptor binding and HERG channel affinities for a series of antipsychotic drugs.
2002 Aug 16
[Treatment of tics in Tourette syndrome with atypical antipsychotic drugs].
2002 Aug 5
The effects of long-term testosterone, gonadotropin-releasing hormone agonist and pimozide treatments on testicular development and luteinizing hormone levels in juvenile and early maturing striped bass, Morone saxatilis.
2002 Dec
Neuroleptic withdrawal versus serotonergic syndrome in an 8-year-old child.
2002 Fall
Differential inhibition of T-type calcium channels by neuroleptics.
2002 Jan 15
The treatment of Tourette's syndrome: current opinions.
2002 Jul
Potassium channel antagonists influence porcine granulosa cell proliferation, differentiation, and apoptosis.
2002 Jul
Trigeminal neuralgia.
2002 Jun
Seasonal short-term effects of naltrexone on LH secretion in male carp (Cyprinus carpio L.).
2002 Mar
Drug interactions of clinical significance for the dermatologist: recognition and avoidance.
2003
P300 changes in major depressive disorders with and without psychotic features.
2003 Feb
Antipsychotic augmentation for treatment resistant obsessive-compulsive disorder: what if antipsychotic is discontinued?
2003 Jan
[A case of delusional parasitosis in severe heart failure. Olanzapine within the framework of a multimodal therapy].
2003 Jul
Pimozide injections into the Nucleus accumbens disrupt maternal behaviour in lactating rats.
2003 Jul
Inhibitory effects of pimozide on cloned and native voltage-gated potassium channels.
2003 Jul 4
Disabling cough: habit disorder or tic syndrome?
2003 Jun 7
Disabling cough: habit disorder or tic syndrome?
2003 Jun 7
H1-histamine receptor affinity predicts short-term weight gain for typical and atypical antipsychotic drugs.
2003 Mar
Patents

Sample Use Guides

Children: Treatment should be initiated at a dose of 0.05 mg/kg preferably taken once at bedtime. The dose may be increased every third day to a maximum of 0.2 mg/kg not to exceed 10 mg/day. Adults: treatment should be initiated with a dose of 1 to 2 mg a day in divided doses. The dose may be increased thereafter every other day. Most patients are maintained at less than 0.2 mg/kg/day, or 10 mg/day, whichever is less. Doses greater than 0.2 mg/kg/day or 10 mg/day are not recommended. At doses above 4 mg/day, CYP 2D6 genotyping should be performed. In poor CYP 2D6 metabolizers, doses should not exceed 4 mg/day, and doses should not be increased earlier than 14 days.
Route of Administration: Oral
Pimozide (PMZD) (10 uM) had minimal effect on Kv1.4, and had no effect on the M-current candidates, KCNQ2 and KCNQ3 when co-expressed in Xenopus oocytes. In hippocampal neurons, PMZD inhibited the delayed rectifiers by approximately 60%, and A-type currents were insensitive to PMZD. The results suggest that PMZD inhibits certain neuronal Kv channels in heterologous expression systems and in hippocampal neurons. PMZD was less effective on A-type currents, presumably because its ability to block requires a prolonged opening of the K channels.
Substance Class Chemical
Created
by admin
on Sat Dec 16 17:29:47 UTC 2023
Edited
by admin
on Sat Dec 16 17:29:47 UTC 2023
Record UNII
1HIZ4DL86F
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PIMOZIDE
EP   INN   JAN   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD  
INN   USAN  
Official Name English
ORAP
Brand Name English
PIMOZIDE [USP MONOGRAPH]
Common Name English
PIMOZIDE [ORANGE BOOK]
Common Name English
MCN-JR-6238
Code English
Pimozide [WHO-DD]
Common Name English
2H-BENZIMIDAZOL-2-ONE, 1-(1-(4,4-BIS(4-FLUOROPHENYL)BUTYL)-4-PIPERIDINYL)-1,3-DIHYDRO
Common Name English
PIMOZIDE [USAN]
Common Name English
NSC-170984
Code English
PIMOZIDE [MART.]
Common Name English
PIMOZIDE [JAN]
Common Name English
PIMOZIDE [EP MONOGRAPH]
Common Name English
pimozide [INN]
Common Name English
1-[1-[4,4-Bis(4-fluorophenyl)butyl]-4-piperidyl]-2-benzimidazolinone
Systematic Name English
R 623
Code English
PIMOZIDE [MI]
Common Name English
PIMOZIDE [VANDF]
Common Name English
R-6238
Code English
PIMOZIDE [USP-RS]
Common Name English
R-623
Code English
Classification Tree Code System Code
NCI_THESAURUS C29710
Created by admin on Sat Dec 16 17:29:48 UTC 2023 , Edited by admin on Sat Dec 16 17:29:48 UTC 2023
LIVERTOX NBK548846
Created by admin on Sat Dec 16 17:29:48 UTC 2023 , Edited by admin on Sat Dec 16 17:29:48 UTC 2023
WHO-ATC N05AG02
Created by admin on Sat Dec 16 17:29:48 UTC 2023 , Edited by admin on Sat Dec 16 17:29:48 UTC 2023
NDF-RT N0000180182
Created by admin on Sat Dec 16 17:29:48 UTC 2023 , Edited by admin on Sat Dec 16 17:29:48 UTC 2023
WHO-VATC QN05AG02
Created by admin on Sat Dec 16 17:29:48 UTC 2023 , Edited by admin on Sat Dec 16 17:29:48 UTC 2023
Code System Code Type Description
MERCK INDEX
m8816
Created by admin on Sat Dec 16 17:29:48 UTC 2023 , Edited by admin on Sat Dec 16 17:29:48 UTC 2023
PRIMARY Merck Index
LACTMED
Pimozide
Created by admin on Sat Dec 16 17:29:48 UTC 2023 , Edited by admin on Sat Dec 16 17:29:48 UTC 2023
PRIMARY
NCI_THESAURUS
C47672
Created by admin on Sat Dec 16 17:29:48 UTC 2023 , Edited by admin on Sat Dec 16 17:29:48 UTC 2023
PRIMARY
DAILYMED
1HIZ4DL86F
Created by admin on Sat Dec 16 17:29:48 UTC 2023 , Edited by admin on Sat Dec 16 17:29:48 UTC 2023
PRIMARY
DRUG CENTRAL
2172
Created by admin on Sat Dec 16 17:29:48 UTC 2023 , Edited by admin on Sat Dec 16 17:29:48 UTC 2023
PRIMARY
IUPHAR
90
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PRIMARY
MESH
D010868
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PRIMARY
RXCUI
8331
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PRIMARY RxNorm
DRUG BANK
DB01100
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PRIMARY
PUBCHEM
16362
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PRIMARY
NSC
170984
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PRIMARY
CHEBI
8212
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PRIMARY
EPA CompTox
DTXSID8023474
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PRIMARY
EVMPD
SUB09847MIG
Created by admin on Sat Dec 16 17:29:48 UTC 2023 , Edited by admin on Sat Dec 16 17:29:48 UTC 2023
PRIMARY
ECHA (EC/EINECS)
218-171-7
Created by admin on Sat Dec 16 17:29:48 UTC 2023 , Edited by admin on Sat Dec 16 17:29:48 UTC 2023
PRIMARY
RS_ITEM_NUM
1539508
Created by admin on Sat Dec 16 17:29:48 UTC 2023 , Edited by admin on Sat Dec 16 17:29:48 UTC 2023
PRIMARY
WIKIPEDIA
PIMOZIDE
Created by admin on Sat Dec 16 17:29:48 UTC 2023 , Edited by admin on Sat Dec 16 17:29:48 UTC 2023
PRIMARY
SMS_ID
100000081975
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PRIMARY
CAS
2062-78-4
Created by admin on Sat Dec 16 17:29:48 UTC 2023 , Edited by admin on Sat Dec 16 17:29:48 UTC 2023
PRIMARY
FDA UNII
1HIZ4DL86F
Created by admin on Sat Dec 16 17:29:48 UTC 2023 , Edited by admin on Sat Dec 16 17:29:48 UTC 2023
PRIMARY
INN
2330
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PRIMARY
ChEMBL
CHEMBL1423
Created by admin on Sat Dec 16 17:29:48 UTC 2023 , Edited by admin on Sat Dec 16 17:29:48 UTC 2023
PRIMARY
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